Pelargonin

Pelargonin
Names

IUPAC name 7-Hydroxy-2-(4-hydroxyphenyl)-3,5-bis{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-benzopyran-1-ylium
Other names Pelargonidin 3,5-di-β-D-glucoside
Identifiers
CAS Number	17334-58-6^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:133365^Y
ChemSpider	390369
ECHA InfoCard	100.037.584
KEGG	C08725^Y
PubChem CID	441772
UNII	4OJV6238UJ^Y
CompTox Dashboard (EPA)	DTXSID00938359
InChI InChI=1S/C27H30O15/c28-8-17-19(32)21(34)23(36)26(41-17)39-15-6-12(31)5-14-13(15)7-16(25(38-14)10-1-3-11(30)4-2-10)40-27-24(37)22(35)20(33)18(9-29)42-27/h1-7,17-24,26-29,32-37H,8-9H2,(H-,30,31)/p+1/t17-,18-,19-,20-,21+,22+,23-,24-,26-,27-/m1/s1 Key: SLCKJKWFULXZBD-ZOTFFYTFSA-O InChI=1/C27H30O15/c28-8-17-19(32)21(34)23(36)26(41-17)39-15-6-12(31)5-14-13(15)7-16(25(38-14)10-1-3-11(30)4-2-10)40-27-24(37)22(35)20(33)18(9-29)42-27/h1-7,17-24,26-29,32-37H,8-9H2,(H-,30,31)/p+1/t17-,18-,19-,20-,21+,22+,23-,24-,26-,27-/m1/s1 Key: SLCKJKWFULXZBD-OJOSBQBKBL
SMILES c1cc(ccc1c2c(cc3c([o+]2)cc(cc3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
Properties
Chemical formula	C₂₇H₃₁O₁₅⁺
Molar mass	595.53 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Pelargonin is an anthocyanin. It is the 3,5-O-diglucoside of pelargonidin.

Natural occurrences

Pelargonin is a pigment, found in barberries,^[1] the petals of the scarlet pelargonium flower^[2] pomegranates,^[3] and red wine.^[4]

References

^ Duke, James (1992). "Berberis vulgaris (Berberidaceae), United States Department of Agriculture, National Agricultural Library: Dr. Duke's Phytochemical and Ethnobotanical Databases". phytochem.nal.usda.gov.
^ Saunders Currey, Geoffrey (1922). "The Colouring Matter of the Scarlet Pelargonium". J. Chem. Soc., Trans. 121: 319–323. doi:10.1039/CT9222100319.
^ Gil, M.I.; Cherif, J.; Ayed, N.; Artes, F.; Tomasbarberan, F.A. (1995). "Influence of Cultivar, Maturity Stage and Geographical Location on the Juice Pigmentation of Tunisian Pomegranates". Zeitschrift für Lebensmittel-Untersuchung und Forschung. 201 (4): 361–364. doi:10.1007/BF01192733. S2CID 95566626.
^ He, Fei; Liang, Na-Na; Mu, Lin; Pan, Qiu-Hong; Wang, Jun; Reeves, Michael J.; Duan, Chang-Qing (February 2012). "Anthocyanins and Their Variation in Red Wines I. Monomeric Anthocyanins and Their Color Expression". Molecules. 17 (2): 1571–1601. CiteSeerX 10.1.1.399.2775. doi:10.3390/molecules17021571. PMC 6268338. PMID 22314380.

External links

Anthocyanidins and their anthocyanin glucosides

3-Hydroxyanthocyanidins

3-Deoxyanthocyanidins

O-Methylated anthocyanidins

Anthocyanins
(anthocyaninidin glycosides)

Glucosides:

Callistephin (Pelargonidin 3-O-glucoside)
Chrysanthemin (Cyanidin 3-O-glucoside)
Myrtillin (Delphinidin 3-O-glucoside)
Oenin (Malvidin 3-O-glucoside)
Peonidin 3-O-glucoside
Petunidin 3-O-glucoside
Pulchellidin 3-glucoside

Diglucosides:

Cyanin (Cyanidin 3,5-O-diglucoside)
Delphin (Delphinidin 3,5-O-diglucoside)
Malvin (Malvidin 3,5-diglucoside)
Pelargonin (Pelargonidin 3,5-O-diglucoside)
Peonin (Peonidin 3,5-O-diglucoside)
Petunin (Petunidin 3,5-O-diglucoside)

Others glycosides:

Antirrhinin (Cyanidin 3-O-rutinoside)
Ideain (Cyanidin 3-O-galactoside)
Delphinidin 3-O-rhamnoside
Petunidin 3-O-arabinoside
Petunidin 3-O-galactoside
Petunidin 3-O-rhamnoside
Petunidin 3-O-rutinoside
Primulin (Malvidin 3-O-galactoside)
Pulchellidin 3-rhamnoside
Tulipanin (Delphinidin 3-O-rutinoside)

Acylated anthocyanins

Acetylated anthocyanins	Cyanidin 3-O-(6-acetyl)glucoside Delphinidin 3-O-(6-acetyl)glucoside Malvidin 3-O-(6-acetyl)glucoside Petunidin 3-O-(6-acetyl)galactoside Petunidin 3-O-(6-acetyl)glucoside Peonidin 3-O-(6-acetyl)glucoside
Coumaroylated anthocyanins (cis- and trans-)	Cyanidin 3-O-(6-p-coumaroyl)glucoside Delphinidin 3-O-(6-p-coumaroyl)glucoside Malvidin 3-O-(6-p-coumaroyl)glucoside Petunidin 3-O-(6-p-coumaroyl)glucoside Peonidin 3-O-(6-p-coumaroyl)glucoside
Caffeoylated anthocyanins	Malvidin 3-O-(6-p-caffeoyl)glucoside Peonidin 3-O-(6-p-caffeoyl)glucoside
Malonylated anthocyanins	Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
Acylated anthocyanin diglycosides	Cyanidin 3-O-(di-p-coumarylglucoside)-5-glucoside Gentiodelphin (delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside)) Nasunin (Delphinidin 3-(p-coumaroylrutinoside)-5-glucoside) Petanin (petunidin 3-[6-O-(4-O-(E)-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-D-glucopyranoside]-5-O-β-D-glucopyranoside) Violdelphin (Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside)

Flavanol-anthocyanin adducts

Miscellaneous

Metalloanthocyanins (commelinin)
Cyanosalvianin
Protocyanin
Protodelphin)
Pyranoanthocyanins
Copigmentation
Anthocyanone A (degradation product of oenin)
Malvone (oxidation product of malvin)

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